Top Tech Jobs & Startup Jobs in Chicago, IL

Supports back-office trading operations by reconciling trades, positions, and profit and loss; maintaining trading data quality; investigating issues with trading desks and clearing firms; assisting with month-end reporting; improving operational processes; and completing firm initiatives and ad hoc projects.

Lead product vision, roadmap, and delivery for trading platforms, tools, and AI agents. Define agent autonomy, trust controls, and human-in-the-loop workflows while improving trader performance, efficiency, and risk outcomes. Build and lead a lean product team, partner with engineering, risk, compliance, and legal, and establish an agent-native product operating model that can scale across PEAK6 businesses.

Oversee global employee benefits strategy, administration, compliance, vendor relationships, open enrollment, retirement plans, leave programs, and employee communications. Lead benefits plan evaluation, regulatory activities, audits, system administration in Workday, data analysis, and process improvements across U.S. and international locations. Manage benefits team members and collaborate with HR, payroll, finance, brokers, carriers, and third-party administrators.

Coordinate enterprise-wide learning and management development programs across PEAK6 and its subsidiaries. Manage program calendars, logistics, communications, participation tracking, reporting, and continuous improvement. Source, vet, and oversee external training vendors, facilitators, coaches, and content providers, including contracts, budgets, deliverables, and performance. Administer Workday Learning, maintain courses and learning paths, manage compliance training, and provide completion reports. Partner with HR leaders and business stakeholders on talent development initiatives.

Manage the Delta One portfolio, including trading activity, balance sheet and RWA utilization, funding costs, portfolio financing, and P&L reporting. Build and maintain pricing, position-management, and attribution tools using Python and SQL. Partner with Risk, Finance, Operations, and banking partners on margin efficiency, capital movement, cash management, and financing decisions. The role also supports expansion of the Middle Office function across PEAK6 entities.

Supports and integrates SaaS and cloud-based business applications across PEAK6. Responsibilities include architecting cloud offerings, managing technology investments, implementing SaaS integrations, provisioning applications, developing support processes and documentation, evaluating software platforms, and enabling business operations through technology. The role also provides white-glove employee support and requires strong communication, problem-solving, and cloud administration skills.

Own product roadmaps and execution for trading tools, collaborate with traders and engineers to define user stories and acceptance criteria, prioritize backlogs, run usability testing, track KPIs, and drive product improvements to boost desk performance and efficiency.

Lead end-to-end bi-weekly multi-state payroll processing in Workday Payroll across multiple entities; ensure compliance with federal/state laws; manage payroll tax registrations and notices; serve as SME for payroll inquiries; drive year-end W-2 processing, reconciliations, reporting, GL entries, and process improvements; partner with HR, Finance, auditors, and system implementations to maintain controls and automate payroll workflows.

Process bi-weekly multi-state payroll via Workday for exempt and non-exempt employees; manage payroll tax registrations and notices; support year-end W-2s and external audits; reconcile payroll bank transactions and GL accounts; partner with HR, Finance, and Treasury; create ad hoc reporting and drive payroll process improvements and automation.

Lead product roadmaps and execution for internal HR, Finance, and support tools. Partner with cross-functional teams to define user stories, prioritize backlogs, measure impact, run usability testing, and iterate on AI-enabled and SaaS solutions to improve performance and efficiency.